1,1,1-trifluoropent-4-en-2-ol

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2,4-difluorobenzoate (1.72 g, 9.99 mmol) was dissolved in dioxane. To this was added 1,1,1-trifluoropent-4-en-2-ol (1.40 g, 9.99 mmol) followed by 60% (mineral oil) NaH (0.40 g, 9.99 mmol). The resulting mixture was heated to 90° C. and stirred overnight. After cooling to RT, 1N HCl was added and the mixture transferred to separatory funnel. The mixture was extracted with ethyl acetate after which the organic solution was washed with 1N NaOH (2 times) and sat'd NaCl. The solution was dried over Na2SO4, filtered and the solvent removed to yield the title compound as an oil which was used in the next step without further purification. After cooling to RT the mixture transferred to separatory funnel The mixture was extracted with ethyl acetate after which the organic solution was washed with 1N NaOH (2 times) The solution was dried over Na2SO4 filtered the solvent removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of indium powder (2.3 g, 20 mmol) in water is added allyl bromide (2.5 mL, 30 mmol) followed by trifluoroacetaldehyde ethyl hemiacetal (1.3 mL, 10 mmol). The reaction mixture is stirred for 16 h and then extracted with t-butyl methyl ether (50 mL). The organic layer is washed with water, brine, dried with Na2SO4 and concentrated to give the title compound as a colorless oil. extracted with t-butyl methyl ether (50 mL) The organic layer is washed with water, brine dried with Na2SO4 concentrated

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2,4-difluorobenzoate (1.72 g, 9.99 mmol) was dissolved in dioxane. To this was added 1,1,1-trifluoropent-4-en-2-ol (1.40 g, 9.99 mmol) followed by 60% (mineral oil) NaH (0.40 g, 9.99 mmol). The resulting mixture was heated to 90° C. and stirred overnight. After cooling to RT, 1N HCl was added and the mixture transferred to separatory funnel. The mixture was extracted with ethyl acetate after which the organic solution was washed with 1N NaOH (2 times) and sat'd NaCl. The solution was dried over Na2SO4, filtered and the solvent removed to yield the title compound as an oil which was used in the next step without further purification. After cooling to RT the mixture transferred to separatory funnel The mixture was extracted with ethyl acetate after which the organic solution was washed with 1N NaOH (2 times) The solution was dried over Na2SO4 filtered the solvent removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of indium powder (2.3 g, 20 mmol) in water is added allyl bromide (2.5 mL, 30 mmol) followed by trifluoroacetaldehyde ethyl hemiacetal (1.3 mL, 10 mmol). The reaction mixture is stirred for 16 h and then extracted with t-butyl methyl ether (50 mL). The organic layer is washed with water, brine, dried with Na2SO4 and concentrated to give the title compound as a colorless oil. extracted with t-butyl methyl ether (50 mL) The organic layer is washed with water, brine dried with Na2SO4 concentrated